How the founder of Zillow and Hotwire led his startups through major crises, layoffs, and a down round to massive exits

Spencer Rascoff is the CEO of Zillow, a real-estate website and app. Before that, he helped create and lead the travel website Hotwire.

Zillow went public in 2011 and has grown tenfold since. Today, the company generates over $1 billion in annual revenue; it has made 16 acquisitions and has 3,500 employees.

Rascoff led both Hotwire and Zillow out of crises to success after making deep cuts and recommitting the companies' original missions.

Spencer Rascoff knows a lot about running a company during a crisis.
He’s the CEO of Zillow, which he ran through the housing crash. That was after he ran Hotwire, which survived the dot com crash only to learn it sold plane tickets to the 9/11 hijackers.
"There's the shadow of this weird connection to the actual tragedy itself, and then from a business standpoint, basically nobody traveled for like six months," Rascoff said on Business Insider's podcast, "Success! How I Did It." "And so it was a very difficult time and we had significant layoffs."
Through personal and professional tragedies, Rascoff and his companies bounced back. Zillow now has a market cap that exceeds $5 billion. On this episode, Rascoff tells how he did it. Plus, he tells what Uber’s new CEO is like (they worked together twice), and what it was like touring with rock bands as a kid.
You can listen to the podcast below:

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Hearst Magazines CCO Joanna Coles

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Following is a transcript of the podcast, which has been lightly edited for clarity and length.Business InsiderAlyson Shontell: We’re really happy to have you today. Thanks so much, Spencer.Spencer Rascoff: Thank you. I'm excited to be here.Shontell: Can you take me back to growing up — what it was like for you? I understand you were an athlete and a chess whiz, and your dad had an awesome job.Rascoff: I grew up here in Manhattan through fifth grade. My dad was an entrepreneur in the rock-and-roll industry, which I'll tell you about, and my mom was a real-estate agent and then a schoolteacher. I had a terrific upbringing.
I was really academic, was a nationally ranked chess player and played really competitively. I was the fourth-best chess player in the country when I was a little kid and played every weekend really hardcore. Then we moved to LA, and my eyes were opened to this whole other world of possibilities where you could go swimming and play basketball and play sports, and so my whole worldview changed.
From an early age, I was inspired by my dad's entrepreneurialism. My dad was a partner at an accounting firm, one of the Big Eight accounting firms, now is part of KPMG. And in 1972, when he was just a young partner there, this white-shoe, New York, early-'70s accounting firm told the manager of the Rolling Stones, Prince Rupert Loewenstein, to take a hike. "We're not going to be the accountants for a bunch of rock-and-roll, drug-addicted crazy people." And my dad thought that sounded pretty interesting actually.
And so he took a leave of absence from the accounting firm and became the tour accountant on the 1972 Rolling Stones tour. And this was a couple years before I was born. That started his career, which spanned decades in rock-and-roll and ultimately he was a tour producer, a business manager of the Rolling Stones, U2, David Bowie, Pink Floyd, Paul Simon, and many others.
Watching that experience and growing up in and around the rock-and-roll industry and watching him leave a pretty conservative industry of accounting for the music industry — and the innovation that he brought to that industry — was a big part of my upbringing.Shontell: When you see someone take a big risk like that and then ultimately become successful at it, I have to imagine it makes you feel like you could tackle a lot as well.Rascoff: Yes, for sure.Shontell: From what I understand, you had a pretty awful family tragedy happen early. Did that shape your career?Rascoff: Definitely.
When I was 15 and my brother was 17, he passed away in a car accident just a couple days before graduating from high school, and obviously it changed me dramatically. It made me grow up real fast. But it also kicked me into a different gear in terms of my quest for achievement.
Prior to that, I hadn't experienced much grit in my life. I grew up pretty affluent — frankly — spending summers touring with rock bands in Europe and in Asia with my family. And then when you lose your brother at an early age, all of a sudden you're sort of jolted into just a different world. Those last couple of years of high school, I kind of felt like I had to really overachieve, and I worked really hard and am still working really hard 25 years later.
Winding up on Wall StreetWikipediaShontell: You went off to Harvard, and then you did what a lot of Harvard people seem to do: You wound up on Wall Street.Rascoff: Too many, in my opinion.
So I graduated from Harvard, class of '97, and the internet was just a couple years old then and, of my graduating class of about 1,600, probably fewer than 10 people moved out West to work in tech. They went to companies like AltaVista and Excite and Yahoo and eBay, which were tiny little startups at the time. Honestly, if you ask them why they did it, I think most of them would say it's because they couldn't get jobs in consulting or investment banking at the time. Of course these people went on to incredible careers and massive riches from having been so early in technology.
But back then, the Ivy League was just this conveyor belt to Wall Street. And, in my opinion, unfortunately, not that much has changed actually, 20 years later. A huge amount of our intellectual capital just gravitates there, really not out of passion for those industries but just because they don't know what else to do when they graduate from college. And I think that's unfortunate. I did my two years and couldn't wait to get out of there.Shontell: When you were realizing that the Wall Street and finance world was not for you, you said your wife helped point things out before you even realized that you're unhappy doing something.Rascoff: Yeah, I call this a "career mirror."
I think it's incredibly important for everyone to have a career mirror. It can be a spouse, a friend, a parent, but it has to be somebody that's far enough away from you that they're not in the super day-to-day — like it can't really be a coworker — but they have to be close enough to know you better than you know yourself.
Every career decision I've made has been because my wife told me to, because she's held up a mirror to me. She said: "Look, you're unhappy. You may not realize it, but you're unhappy doing this thing." And when I left Goldman Sachs to go to private equity, and I left private equity to do a startup, when I left that startup to do another startup, every one of those career changes was because she saw something before I did about how I was feeling.
Launching HotwireCourtesy of ZillowShontell: So talk to me about the move from private equity into your startup, Hotwire. It ended up being a huge success. Everyone remembers it. So tell me about how that got formed.Rascoff: When I got to TPG, which is a huge private-equity firm, in 1999 after I left Goldman Sachs, the private-equity firms were sort of on their heels. But the smart thing that the private firms did was they looked at their existing portfolio companies and tried to figure out how to leverage the internet.
And so in the case of TPG, we had bought Continental Airlines out of bankruptcy, America West Airlines out of bankruptcy, Ryan Air, which is the largest airline in Europe, and we had sold much of the Continental stake to Northwest, so by the time I got there, in the late '90s, we basically controlled four airlines.
And so Hotwire was born out of TPG, saying to these airlines and then a couple of other airlines: "Hey, let's create an industry consortium startup to compete with Priceline." I was basically staffed on that project, and I eventually left TPG to start the company. We had to call it something cool, and so we called it "Project Purple Demon" because that sounded really hip and this was San Francisco, 1999, you had to sound cool to attract employees, and Project Purple Demon would eventually become Hotwire.
And the little-known fact is that, at the same time, those airlines that we went to, to create the company, said: "Hey, this sounds great. We're going to create an airline-industry-controlled and -owned consortium startup in the discount- travel space to compete with Priceline. Will you, TPG, also create one in the full-price category to compete with Travelocity and Expedia?"
And the project name for that was T-2, which stood for "Travelocity Terminator." And we said: "No, we don't really do this. We're a private-equity firm already kind of out of our depth doing this one startup."
And so the airlines hired Boston Consulting Group to create T-2, which would eventually become Orbitz. So these two companies, Orbitz and Hotwire, were started at about the same time by about the same airlines but had very different governance. In the case of Orbitz, the airlines controlled Orbitz, and in the case of Hotwire, the airlines all got non-voting stock, and so the management team had latitude on how to run Hotwire.
For example, Hotwire pivoted very quickly to the hotel side of the business, which is where most of the money is in the travel industry. But in the case of Orbitz, they stuck with airline tickets because the airlines wanted Orbitz to basically be a foil to Expedia and Travelocity. Fifteen-plus years later, you probably still think of airlines when you think of Orbitz and you probably think of hotels when you think of Hotwire. The airlines wanted it to be that way. Of course, now they're all owned by Expedia Group, which is who we sold Hotwire to and, ironically, who Orbitz eventually sold to as well. So Expedia Group owns Orbitz, Travelocity, Expedia, Hotwire, Hotels.com, Trivago, and basically everything.
Leading through adversityAPShontell: So you started what eventually became Hotwire, in the late '90s. Prime dot-com boom.Rascoff: Bubble.Shontell: And then in 2001, obviously 9/11 happened, and that rocked the entire industry, but you were in the travel industry and it really hit your business hard. So talk about that, because it also sounds like, from what I understand, you all discovered that you personally had a role, unintentionally, in that day.Rascoff: You know, 9/11 really tested the company for a lot of reasons.
So first off, for me personally, I was in New York on September 10. I spoke at the Millennium Hilton at World Trade Center, which was, of course, crushed the next day. I was on the Newark-to-SFO flight on the 10th — or maybe I'm off by a day — but within a day or two on the same flight, same flight number, and so I was personally shaken up by my connection to it, and I actually lost a family friend on the plane that went down in Pennsylvania, and so that was obviously difficult. And then that morning we had tens of thousands of customers who were stranded around the world, who we had sold airline tickets and hotel rooms to. So we had this huge customer-service nightmare. And then to make matters worse, as you alluded to, Hotwire actually sold some of the tickets to the hijackers.Shontell: How did you realize that? And what was it like when you put that together?Rascoff: Not that it makes much difference, but it wasn't the September 11 flights, it was the flights a couple of days earlier that put the team in place in Bangor, Maine, and then they flew from Bangor to Logan. I think the way we found out about it was the FBI told us, they came knocking, I think, probably that day or within a couple of days. And it cast this really awful shadow of culpability over the company. So as we were struggling with dislocated customers, employees who we weren't sure of their location, and then there's the shadow of this weird connection to the actual tragedy itself. And then from a business standpoint, basically nobody traveled for, like, six months.
And so it was a very difficult time, and we had significant layoffs. We did a down round, which wiped out a lot of the equity that the employees had in the company. To our credit, two years later we had turned the company around and pulled through all of that trauma and sold the company successfully to Expedia for about $700 million.Shontell: In all cash.Rascoff: In all cash, which at the time — this is so quaint, right? — in 2003, when we sold the company, that was the largest-ever all-cash sale of a tech company. You know, now $700 million is just like an Uber series E round.Shontell: So coming back from that, it must have been hard because it rocked your business, and every tech business was rocked hard, and coming back to that kind of exit. I mean, how did you do that?Rascoff: The team stuck together.
I mean, the first thing we did was we cut deep at the company, and I've done layoffs, unfortunately, twice in my career, once at Hotwire and then once at Zillow. I think it's important to cut deep enough that you never have to have a second round of cuts, if possible, because the fear of, "Oh, am I going to be next?" It just paralyzes the organization, so we cut probably deeper than we had to, intentionally, to leave some cushion, and we recommitted the employee base to the mission and to each other.
You made me talk about my brother, but I guess it's not that different than that, it's like, "Now we have to sort of succeed so that those that are no longer here didn't sacrifice what they sacrificed in vain." And so we worked our butts off to make Hotwire successful. We did a lot of really smart tactical business-oriented things around the pivot to hotels, around innovations in the product.
At the time, Priceline was our main rival and the "name your price" thing Priceline's innovation, and Hotwire's innovation was that we showed you the price, and so you didn't know what the hotel was until after you purchased, but we showed you what the price was and so it took some of the guessing out of it. And that was very innovative and it made for a very appealing value proposition to our suppliers, our airlines and hotels, but also to consumers.
And then we took a big bet on advertising. One of the benefits of the dot-com meltdown was TV advertising was pretty cheap because all those startups that were advertising in the late '90s were gone. And so at Hotwire, we invested really early in TV. Today, of course, you turn on the TV and two seconds later you'll see an ad for Trivago and Expedia and Tripadvisor, they're everywhere. But in 2001 to 2003, the airwaves were pretty empty from travel advertising and that was a big bet that we made, and it paid off.Shontell: So when you're selling the company, it sounds like a huge, amazing exit. Was it was great for you guys as founders or was it not?Rascoff: It was not. And this is a good lesson for founders: a down round basically wipes out most of the employee equity because employees typically have common and investors typically have preferred, so a $700 billion sale sounds really great but it's mostly the venture capitalists that made the money, not the employees. You don't have to feel sorry for anyone at Hotwire, they all did fine and they're doing fine. But it wasn't the type of exit that I think people expected.Shontell: Right, it's not like when you read, "Twenty-five year old sells his company for $700 million in all cash."Rascoff: Read the fine print, or it usually doesn't get printed as fine print, but usually stories like that have a little layer of complexity to them.
Working with Dara KhosrowshahiReutersShontell: So you go on and you become a VP at what is now Expedia.Rascoff: Yeah, so the two years prior to the sale, from 2001 to '03, those two difficult years after 9/11. I was actually commuting to Seattle because on September 10, 2001, my wife moved from San Francisco, which is where Hotwire was, to Seattle to go to med school at the University of Washington. Our first day apart was September 11, and I remember watching it on TV from San Francisco and on the phone with her in Seattle. So for those two difficult years, I was also commuting to my wife from San Francisco to Seattle. As soon as we sold the company to Expedia, which is based in Seattle, I moved, like, literally that week, and I worked at Expedia and I managed the hotel business for Expedia, Hotwire, and Hotels.com. And I was there for about a year.Shontell: And you worked with Dara, who is now the Uber CEO, right?Rascoff: I worked with Dara, who I'd known. Everything kind of comes full circle.
When I was a summer analyst at Allen and Co., when I was 19 and in college, he was at Allen and Co. as a junior investment banker and he was my mentor at Allen and Co., so I had known Dara since I was a teenager really. And in the weird small world that it is, he ended up being my manager at Expedia when he was the CEO at Expedia. And so I reported to Dara and he's a fantastic person, executive, manager, mentor, friend. I think the world of him and he's the right choice for Uber. He's exactly what they need right now.Shontell: So you're basically saying I should have called you two months ago and you would have known that this was happening when none of the world did.Rascoff: It was. And I was surprised how surprised everyone was.
I mean, and that's actually a testament to Dara; it's because he is not a self-promoter. Most people probably never heard of Dara Khosrowshahi until the Uber announcement, and that's because he would have it no other way.
So I report to Dara at Expedia, but I wasn't that happy. I wanted to be in a smaller company environment, more entrepreneurial, where I could make more of an individual difference. And so in 2005 I left with most of the Expedia management team that preceded Dara, and we all left to start Zillow together. So the first probably 15 or 20 employees at Zillow all came from Expedia, and that's basically the founding team from Expedia.
Imagining a price on every roofZillowShontell: So were you, like, "Hey, I think let's do this Zillow thing."Rascoff: Five or six or seven of us were just literally in that conference room for weeks discussing, debating, thinking, talking, writing on whiteboards, trying to decide whether to do something in real estate or something else.
We knew we wanted a startup; we knew we wanted to do it together.
We ultimately decided that the consumer need was so great in real estate that consumers were so disempowered. There was this information asymmetry between consumers and professionals in real estate, and so we thought we could apply some of the same themes around information empowerment. However, there's a huge difference that frequently gets lost in the details. In the case of travel, it's a really simple transaction and you don't need an intermediary. You can buy an airline ticket from Expedia or Hotwire and you don't need to talk to anybody. In the case of real estate, it's a complex, infrequent, expensive, emotional transaction, and so I believe it will always have an intermediary, always have a real-estate agent in the transaction.
So at Zillow, we never, even from the very beginning, we never endeavored to eliminate the real-estate agent. We just wanted to provide the consumer with the same information as the real-estate agent and then let them work together. It's much more akin to a WebMD, where there's all this information about health care, and the patient and the patient's family can read it, but then they still go to the doctor and the doctor helps them interpret that information. They're not cutting out the doctor; they're just informing the patient.Shontell: So what's the first product iteration of Zillow like? And how do you start getting early traction for it?Rascoff: I still remember we were in this high-rise at 2 Union St., in downtown Seattle, and we're looking at Queen Anne, which is this neighborhood on a hill that looks at downtown on one side and Puget Sound on the other. And when you look at Queen Anne from the high-rise of this conference room, you can see this landscape of hundreds of houses, and we said: "Every other real-estate site focuses on what's for sale. What if we focused on answering this other question that people have about real estate, which is, 'What's my house worth?'"
And we looked at Queen Anne, and we envisioned "Imagine a price on every rooftop." Wouldn't that be amazing?
And then to further the Seattle part of the story here — this is very Seattle, so indulge me for a second as we sit here in midtown Manhattan, feels a world away. Whales in Puget Sound frequently breach. And so as they pass from Mexico and California up to Alaska during whale season; you can actually see them from offices in Seattle, you can literally see whales in Puget Sound, which is, like, can you imagine a whale in the East River? It's weird to imagine.
But anyway, so we talked a lot about whales and we said, "When you go whale watching and a whale breaches, a whale jumps up above the water, everybody oohs and aahs and takes pictures of it and talks about "Oh, look at the whale," and then the whale goes back under water for like 45 minutes, and it's the most boring thing in the world. You have no idea where the whale went. And that struck us as a lot like housing.
When a home comes on the market, everyone talks about it, you take pictures — "Oh, did you see the neighbor's house?" — but then the home goes off the market and there's no conversation about it. But actually a lot of interesting stuff is happening when that whale is under water, and to the home when it's not on the market. We tried to provide transparency to the whole real-estate marketplace, not just the 3% of homes that are for sale at any point in time. So shine a light on what's happening when the whale is under water was kind of inspiration for us.Shontell: And that was the Zestimate.Rascoff: Yes.
We said: "OK, let's try to figure out what every house in the country is worth. Great. OK. How do we do that? Well I know — let's call Stan," and literally we called Dr. Stan Humphries, who was running analytics and personalization at Expedia, and we called him up and we said, "Stan, we finally figured out what we want to do. We want to figure out what every house in the country is worth, and we want you to be the person who helps us do that." And he said, "Well, I don't know anything about real estate." And we say: "It's OK, this is not about real estate. This is a math problem. It has nothing to do with real estate."
And we went about the task of assembling all this data from county sources. So most of this information — bed, bath, square footage, tax assessment, sale history — is available in county courthouses, but we had to go acquire it, digitize it, and then build the data layer, the Zestimate, that sits on top of that.
And when we launched in — I think it was February 2006 — we got about a million visitors within the first day. Even all these years later, I still don't think any other service — Snapchat, Facebook, whatever — I don't think anyone else has had a million users in day one because it's so cool and so innovative to say, "Oh, my god, I can grab my kid's school roster and I can Zillow everybody at my kid's school and see what everyone's house is worth, see what everyone paid for the home." That was just, like, this, "Oh, my God" kind of thing that launched the company in 2006.Shontell: So you launched Zestimate. Was there press around it? Were headlines writing themselves?Rascoff: Massive press.
I was the CMO at the time, and I met with Henry Blodget at Business Insider — it was a small operation back then — and we met with Walt Mossberg at The Wall Street Journal and we met with Bob Tedeschi at The New York Times and on and on. We briefed them, under embargo, and they were Zillowing their house and they were Zillowing the houses they grew up in on the test site.
Then, the day we launched, there was this huge media explosion, and it brought the site down. So the good of this huge amount of traffic was, well, we launched with a bang, but about six hours later, the website crashed and was down for about four or five hours before we could scramble to get it back up.Shontell: And did you have a patent on it? Was that important?Rascoff: We filed probably a couple of dozen patents, including different things around the Zestimate, but to be candid, we've never really over invested in patent protection because it's the type of thing in technology that it's very hard to rest on. You can have a patent for something and then a couple of other companies violate that patent and then you get relief six years later, but by then it's too late. It's like, "Well, what good is that?" It wouldn't save the day, we don't think.Courtesy of ZillowShontell: It sounds like you have this amazing initial day of launch that any startup would kill to have, by having this innovative piece of technology that you've built. But then a couple of years later, 2008 happens, and you're back in another crash.Rascoff: Yeah, history repeats itself. I'm starting to think maybe I'm the problem.Shontell: Maybe the businesses you start should give us all a sign.Rascoff: No, it's true.
Almost two years to the day from launch, in both cases — Hotwire, '99 to '01, and Zillow, '06 to '08 — these companies hit just a huge brick wall and from an exogenous event totally out of our control. Now, at least in this case, we called it, we saw it coming. You can still go back and you can look on the Zillow blog and see posts that I wrote, and Stan, who by this point had become our chief economist, wrote about how it was obvious, in our opinion, that housing was going to crash and that it was built on the foundation of sand and there was too much easy credit that had allowed people to buy homes who really couldn't afford them. And so our data was predicting it. Unfortunately for us, we didn't short housing or anything like that. We could have probably done very well if we had acted on our data, but we didn't.
Anyway, we saw it coming but that was little consolation. Housing still crashed, we still had layoffs, we avoided a down round this time, though, and that is not insignificant. And as was the case with Hotwire, within another year or two, we got up off the mat and were doing well. It was the same thing: It was cut deep and recommit the remaining employees to the mission. In both cases, the adversity that Hotwire and Zillow faced, there was a silver lining, it turns out, it made both companies much stronger as a result, and I don't think Zillow would have been as successful today had it not been for the adversity that we faced in '07, '08.
Growing ZillowCourtesy of ZillowShontell: So from there you took the company public in 2011 — your first time taking a company public.Rascoff: I had advised as an investment banker taking other companies public, but certainly the first time as a public CEO, and it was a fun, interesting experience but not the end by any means. I mean, we viewed it very much as just a steppingstone, not the end, but the beginning. We had about $15 million of quarterly revenue, we had about a $500 million market cap when we went public.Shontell: And now you're doing what? A billion?Rascoff: Today, we do about $250 million of quarterly revenue, but over a billion of revenue, and we have about $7 or $8 billion market cap. So the company has grown tremendously: 16 acquisitions and 3,500 employees. When we went public we had about 300 employees. So everything is about 10x today as compared with the IPO about six years ago, and that's been amazing. It's also forced me to totally change everything about how I lead and how I manage and what my calendar looks like and what my day-to-day is because the company is just a totally different animal today than it was six years ago.Shontell: So talk about that. You have a podcast of your own called "Office Hours," and there's an episode with Bill Gurley — a well-known tech investor who has been on your board — that I was listening to. Bill was saying, "It's great when startups can figure out how to grow to be worth tens of millions and then generate hundreds of millions, but it is a Herculean effort to get it from hundreds of millions of revenue to billions." And you've done all that, and now your job is to get it from a billion to more.Rascoff: And it only gets harder.
It's true: The first $100 million of revenue is the easiest. That probably sounds like really callous, but the truth is that it only gets harder. When you have $1 billion in revenue, it's very difficult to grow 25% year over year because you have to invent huge new revenue lines to move the needle. And that's a lot easier off a small base.
The other issue that faces all companies is, as you get to a large enough size, there are people whose job it is to protect business lines — they're just doing their job — but this is the classic case of 'The Innovator's Dilemma," the famous business book, which says that when companies ultimately fail, whether it's Polaroid or whoever, it's not because they were big and dumb; it's because they were actually really smart. They actually were protecting their core; they were doing what you think you're supposed to need to do when you're running a big company, but they don't actually innovate because they're not willing to risk the core, and so they get disrupted. And that is what I spend most of my time worrying about now: We were the disrupter. How do we now avoid being disrupted?Shontell: And most of the money, is it still ads? Is it putting people in touch with a realtor?Rascoff: It's all advertising of different sorts. So about 75% of our revenues — I call it $750-ish million — comes from individual real-estate agents. And then we have a big mortgages business, a rentals business, and a display-advertising business, new construction business, all that together is about a quarter of revenue. But it's all advertising.
Setting yourself up for successCourtesy of ZillowShontell: You touched on this, but you've had to change your leadership style and your whole calendar and everything now that you're running a $7 billion company. How have you figured out how to do that, and what are some things that you've learned?Rascoff: So first of all, you have to take seriously this reflection that for every person at the company, you need to think about, "Is that the right person for the next two years in the role?"
So if you're a manager, you have 10 direct reports; those people, they show up for work today just because they had the job yesterday, but you as their manager need to think, "Is that the right person for the next two years?" And if not, change that person or figure out to change their point of view. But I also think about that for myself, and so I think, "OK, how do I set myself up for what the next two years look like, and what changes do I have to make?"
Everything I say now has a different weight to it, which took some getting used to. I mean, when we were a small startup, I could sort of ask random questions and throw out random ideas. Now people actually do the things I randomly say.Shontell: Your words have weight.Rascoff: Yes, and so realizing that requires me to then change even my questions because questions are really statements in disguise, and even my attendance at things is a vote that I think that thing is important. So being really reflective about those things is something that I've worked hard at. And so it's ongoing.Shontell: All right. So to afford these great big houses, you need to have a successful career. You've had a tremendously successful career. So looking back on it, what would you say has made you the most successful?Rascoff: I've always looked 10 years my senior and tried to find somebody at my company to think about if I want that person's life, their whole life.
Usually, younger people, earlier in their career people, look at a senior person and they look at their compensation, and I'm advising not to do that. So you're an associate in the marketing department, look at the VP of marketing and say, "Do I want her or his work-life balance, respect in the community, intellectual stimulation of their job, title, sure, compensation, yes, but sort of the whole package?" That's the path you're on.
Like, you could wake up in the blink of an eye and end up in that world. And if you don't like that trajectory, then find some other path. The other advice I'd give is something that Sheryl Sandberg has been very articulate about, eloquent about, which is this whole "Your career as a jungle gym not a career ladder." It's something that I found in my career.
So what does that really mean? It means that you're on a particular path and then be willing to go off to the side. So in my case, for example, I was running supplier relations, so relations with the hotel industry, and then I moved over to a marketing role where I really had no experience or background, and then I moved over to a finance role where yet again I had no direct experience. And so it was kind of like one step to the side to take two steps forward, one step back to take three steps forward, and charting this very kind of circuitous route, which is unique to this generation.
I mean, our parents and our grandparents had a much simpler career path, just sort of do the time and you'll get promoted eventually. That's not the way it works now. So you have to build your own career path and be willing to take some steps to the side in order to take steps up.Shontell: Spencer, thank you so much.Rascoff: Thank you.
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Related

Spencer Rascoff knows a lot about running a company during a crisis.
He’s the CEO of Zillow, which he ran through the housing crash. That was after he ran Hotwire, which survived the dot com crash only to learn it sold plane tickets to the 9/11 hijackers.

For more than five years, Uber and Lyft have been locked in a battle to become the ultimate ride-hailing service. Uber has been the leader with a war chest of billions of dollars from investors. But it has come under fire for how it treats drivers and its employees.
Then there's Lyft, which is also worth billions. One of its biggest advantages seems to be its "nice guy" reputation. But it can be hard for nice guys not to finish last.

When Tony Robbins walks into a room, nearly everyone is magnetically drawn to the big guy with a booming voice and a personality to match.
He has used his commanding presence to build a career as the world's most famous life and business coach, helping people like President Bill Clinton, Salesforce CEO Marc Benioff, and the Golden State Warriors.

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Spencer Rascoff is the CEO of real-estate website and app Zillow.
He constantly asks himself the same question about every employee: "Is that the right person for the next two years in the role?"
If the answer is "no," he either changes the person's perspective — or changes the person.

Andrew Toth/GettyTwenty-five years ago, Hearst Magazines executive Joanna Coles was a reporter at The Guardian, covering a court case in which a young woman was jailed for refusing to give evidence against a boyfriend she feared.

Freeform/John Medland"I have literally 25 years of anecdotes," says Joanna Coles.
The chief content officer at Hearst Magazines has served as the editor-in-chief of both Marie Claire and Cosmopolitan magazines. Now, as an executive producer for TV series "The Bold Type," which follows a team of magazine editors, she's drawing on those anecdotes for creative inspiration.